Methylene citryl oxytoluic acid.



RUDOLPH BERENDES AND JliRGEN CAILLSEN, OF ELBERFELD GERMAB IY, ASSIGNORS TO FARBENFABRIKEN VORM. FRIEDR. BAYER dz 00., OF

RATION OF GERMANY.

. Specification of Letters Patent. I

" rate-ma Dee, as, 1%.?

llpplicatios. filed June 11. 1907. sen-a1: 1%. 378.329.

To all whom it may concern:

Be it known that we, Renown Sensuous and JI'JRGEN CALLSEN, doctors of philosophy, chemists, citizens of the German Empire, residing at Ell erfeld, Kingdom of Prussia, Gen many, have invented new and useful Improvements in Methylene Citryl Oxytoluic Acids, of which the following is a specification.

Our invention relates to the preparation of new pharmaceutical products which are chemically methylene citryl oxytoluic'acids having probably the formula:

on coo mcoon According to ourresearches these products possess valuable therapeutic properties and I are suitable for use as medicines for rheumatism,-an average dose being about one grain.

The process for producing our new compounds consists in treating oxytoluic acids (crcsotinic acids) or their salts with the acid dichlorid of methylene citric acid having probably the formula:

on,.coo1

ln-ncom which can be produced by treating methylene citric acid with phosphorus pentachlorid.

The new roducts are crystalline 00111- pounds splitting ofi oxytoluic acid by heat- 111g them with caustic alkalies, being soluble substantially the same therapeutic effect.

In order to illustrate our invention we give the following example, the parts being by Weight: c

roperty of forming salts with.

Example: A solution of 24* parts 05 the acid dic lorid of methylene citric acid in about 300 parts benzene is slowly added to a solution of 304 parts of para-oxytoluic acid (OH:COO'H:CH =1 :2 :4) and 370 arts dimethylanilin in about 3000 arts enaene. The reaction begins at once wit evolution of heat. The reaction mass is allowed. to stand for some hours and is shaken with highly diluted hydrochloric acid about 3 per cent and then with water. After the benzene tilled o'ver'the residue is crystallized from glacial acetic acid. Instead of dimethyl anilinother bases ca able of binding acids,

' such as quinolin, or t e like, may be used.

The methylene citryl ara-oxytoluie acid forms white crystals me tin at fron1.i.75- 178 centigrade. It is odoress and almost tasteless, easily soluble in alcohol and acetone, soluble inbenzene and ether, and scarcely soluble in Water. split oil on heating the new product'with caustic 'alkalies. i

The process is carried out in an analogous manner on using other oxytoluic acids or their salts.

The methylene citryl meta-oxytoluic acid obtained from meta-oxytoluic acid (OH :COOH zfiH =i :2 :5) melts at 179 centigrade. The methylene citryl-ortho-oxytoluic acid obtained from. ortho-oxytoluic acid forms crystals melting at 1O centigrade. t

The methylene citryl. oxy-ortho-toluic acid obtained from oxy-ortho-toluic acid Para-oxytoluic acid 18 ELBERFELD, GERMANY, A 6051 5)- uable therapeutic properties exhibited by the acids, substantially as hereinbefore described.

2. The herein-described new methylene citryl para-oxytoluic acid, obtainable by the action of the acid dichlorid of methylene citric acid upon para-oxytoluic acid, which in the acid form is a white crystalline powder, melting at from 175 to 178 C., soluble in alcohol, acetone, benzene and ether, scarcely soluble in water, and which by heating with caustic alkalies is decomposed into para-oxytoluic acid, forming salts with bases which retain the valuable therapeutic properties exhibited by the acid, substantially as hereinbefore described.

In testimony whereof we have hereunto set our hands in the presence of two subscrib- 15 ing witnesses. 1

RUDOLPH BERENDES. a. SQ]- JURGEN cALLsEN. a. 8.]

Witnesses O'r'ro KoNrc, l-Inco Bo'r'ronER. 

